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345350

(1S)-(+)-(10-Camphorsulfonyl)oxaziridine

Name: (1<I>S</I>)-(+)-(10-Camphorsulfonyl)oxaziridine
Brand: ALDRICH

Synonym(s):

(1S)-(+)-(Camphorylsulfonyl)oxaziridine, (1S)-(+)-2,N-Epoxy-exo-10,2-bornanesultam

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About This Item

Empirical Formula (Hill Notation):

C₁₀H₁₅NO₃S

CAS Number:

104322-63-6

Molecular Weight:

229.30

UNSPSC Code:

12352005

NACRES:

NA.22

PubChem Substance ID:

24861312

MDL number:

MFCD21332910

Beilstein/REAXYS Number:

6274370

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Properties

form

solid

optical activity

[α]28/D +45°, c = 2 in chloroform

impurities

<1% toluene

mp

172-174 °C (lit.)

storage temp.

2-8°C

SMILES string

CC1(C)[C@@H]2CC[C@]13CS(=O)(=O)N4O[C@@]34C2

InChI

1S/C10H15NO3S/c1-8(2)7-3-4-9(8)6-15(12,13)11-10(9,5-7)14-11/h7H,3-6H2,1-2H3/t7-,9+,10+,11?/m1/s1

InChI key

GBBJBUGPGFNISJ-YDQXZVTASA-N

Description

Application

(1S)-(+)-(10-Camphorsulfonyl)oxaziridine can be used:

To convert prochiral ketone enolates into optically active α-hydroxy ketones via enantioselective asymmetric oxidation.
In the synthesis of thymidine oligonucleotides connected through pyrophosphates.
In the asymmetric synthesis of proton pump inhibitors like (R)-Rabeprazole sodium and (R)-Lansoprazole sodium from the corresponding DBU salt of prochiral sulfide.
In the preparation of phosphonoacetate and thiophosphonoacetate oligodeoxynucleotides by oxidizing the corresponding phosphinoacetate.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Chemistry of oxaziridines. 14. Asymmetric oxidation of ketone enolates using enantiomerically pure (camphorylsulfonyl) oxaziridine

Davis FA, et al.

Journal of the American Chemical Society, 112(18), 6679-6690 (1990)

On the synthesis of oligonucleotides interconnected through pyrophosphate linkages

Kistemaker HAV, et al.

European Journal of Organic Chemistry, 2015(27), 6084-6091 (2015)

Davis oxaziridine-mediated asymmetric synthesis of proton pump inhibitors using DBU salt of prochiral sulfide

Mahale RD, et al.

Organic Process Research & Development, 14(5), 1264-1268 (2010)

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Global Trade Item Number

SKU	GTIN
345350-1G	04061826760635